1-(1,3-Dioxolan-2-yl)methanamine → N-[4-({2-[(1,3-dioxolan-2-ylmethyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]-3-fluoro-5-morpholin-4-ylbenzamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[CH2:43][NH2:44]>>[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[CH2:43][NH:44][C:21]1[N:20]=[C:19]([O:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:29]=[C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:31]=[C:2]([F:1])[CH:3]=3)=[CH:9][CH:10]=2)[CH:24]=[CH:23][N:22]=1Participants
3
Procedure
Compound is prepared from 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide and C-[1,3]dioxolan-2-yl-methylamine according to conditions described in general procedure C. Mp: 122-124° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.25-3.30 (m, 6 H), 3.73-3.83 (m, 8 H), 4.19 (bs, 1 H), 6.36 (bs, 1 H), 7.04 (d, J=12.0 Hz, 1 H), 7.26-7.31 (m, 2 H), 7.38-7.61 (m, 5 H), 7.83 (d, J=8.8 Hz, 1 H), 7.99 (d, J=9.2 Hz, 1 H), 8.20 (s, 1 H), 10.46 (s, 1 H).
Sources & evidence
- ORD record
- ord-b8fd633489254cf7b1dd5b16e93dc8ec
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829560B2
Reaction notes
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